


I have waited a lifetime (spent my time so foolishly)

by strideofpride



Category: Gossip Girl (TV 2007)
Genre: Canon Compliant, Multi, Not Chuck Friendly, Post Series, Pre series, bi!blair if you squint, dair endgame, mentions of rape and abuse but nothing graphic, no smut but marking it m for heavier content, serenate if you squint
Language: English
Status: Completed
Published: 2021-02-04
Updated: 2021-02-04
Packaged: 2021-03-15 19:40:58
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,277
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29194713
Author URL: https://archiveofourown.org/users/strideofpride/pseuds/strideofpride
Summary: Technically speaking, Blair’s first kiss is with Serena. Not that she counts that, of course.Dan’s first kiss is with Vanessa. He’s going to be fifteen in two weeks and the best friend he’s ever known has just told him she’s moving to Vermont.Or, Dan & Blair and a series of firsts.
Relationships: Chuck Bass/Blair Waldorf, Dan Humphrey/Blair Waldorf, Dan Humphrey/Georgina Sparks, Dan Humphrey/Serena van der Woodsen, Louis Grimaldi/Blair Waldorf, Nate Archibald/Blair Waldorf, Serena van der Woodsen/Blair Waldorf, Vanessa Abrams/Dan Humphrey
Comments: 16
Kudos: 41





	I have waited a lifetime (spent my time so foolishly)

**Author's Note:**

> This is actually my first GG fic ever!!! I had two totally different Dair fics planned, but then inspiration hit me hard and I figured I should just roll with it and get it all out. I've read practically every Dair fic ever, so if any of it seems familiar to something else, that is why, and I am sorry, I do not mean to steal. Anyway, hope you enjoy!
> 
> TW for mentions of rape and abuse

Technically speaking, Blair’s first kiss is with Serena. Not that she counts that, of course.

It happens one day after school in Blair’s bedroom. There’s only one week left of 6th grade and Serena and Eric are staying with the Waldorfs while Lily is off somewhere exotic and far away with her latest boyfriend. Blair has _Breakfast at Tiffany’s_ on, like always, but Serena is ignoring it, flipping through the latest issue of _Vogue_ instead. As Holly and Paul kiss in the rain and _Moon River_ begins to play, Blair can’t help but turn to Serena.

“S?” Serena raises an eyebrow but does not take her eyes off an article entitled _Supermodel Summer_. “What’s kissing like?”

That gets Serena’s attention. Of course, Serena has already had her first kiss, way back in kindergarten, and many more kisses since. But she’s never really gone into detail about any of them with Blair, other than to tell her which boy and where.

Finally, Serena speaks. “Wet.” Blair scrunches up her nose in disgust and Serena bursts into laughter. “Not in a gross way! Well, not always. Not if the guy is a good kisser.”

“What makes a guy a good kisser?”

Serena ponders that for a moment. “I don’t know really. I guess it’s kinda instinct. Either he knows what he’s doing, or he doesn’t,” Serena says with a shrug.

“I don’t know what I’m doing. I guess that’s going to make me a bad kisser,” Blair says quietly. “Nate won’t want to be with a girl who’s a bad kisser.”

“Hey, Nate’s never kissed anyone either!” Serena lays a comforting hand on Blair’s leg. “For all we know, he could be the bad kisser.”

“He won’t be,” Blair responds with a sigh. “Nate’s too…Nate to be bad at something like kissing.”

With _Breakfast at Tiffany’s_ over, there’s a silence for several minutes as Blair stews in her own insecurity before Serena finally speaks again. “You know…I could show you. How to kiss I mean.”

Blair’s heart starts beating fast and she’s not sure why. “Won’t that be kinda weird?”

Serena shakes her head quickly. “No, no, of course not. It’s just one friend helping another. Think of it as a learning experience. That way you know what to do when Nate finally kisses you.” There’s a weird tone in her voice when she mentions Nate, but Blair pretends not to notice.

“Okay,” Blair nods, wiping her sweaty hands on her skirt. “Let’s do it.”

Serena sits up quickly, moving right next to Blair. She tucks a piece of hair back from Blair’s face and looks right into her eyes. “Are you sure?” Blair nods, unable to get the words out, a first for her.

Serena leans in and tentatively touches her lips to Blair’s. Her lips are soft and a little dry, but it’s not too bad. If Blair was someone else, she might even admit that it was nice. Then Serena’s lips part and Blair feels something wet touch her bottom lip. She realizes with a start it’s Serena’s _tongue_. Not knowing what else to do, Blair opens her mouth in return.

After 15 more seconds, Serena pulls away. “See, that wasn’t bad. You did just fine.”

Blair feels her cheeks grow hot. “That’s it?”

“Yep,” Serena confirms. “That’s all there is to it, really. Some people use more tongue, but I like it like that.” And with that, Serena returns to her magazine as if she hadn’t just kissed her best friend in the whole world.

Three weeks later, Blair kisses Nate for the first time on the porch of his parents’ Hamptons house and spends the rest of her life telling people that was her first kiss instead.

\---

Dan’s first kiss is with Vanessa. He’s going to be fifteen in two weeks and the best friend he’s ever known has just told him she’s moving to Vermont.

Dan sits on his fire escape in shock, trying to process what she just told him. “You’re moving to Vermont? But you love it here! What are you going to do up there, tip cows?” Dan asks bitterly.

“My parents want to move to a commune. And since the law doesn’t allow fifteen-year-olds to be independent, I have to go with them,” Vanessa snarks back.

“What about Ruby? Can’t you just live with her?” To be honest, Vanessa’s older sister has always terrified Dan a little bit with her whole shaved head, rock n’ roll, “I hate men” lifestyle. But he’s desperate for Vanessa to stay. Private school has been rough enough without her there by his side every day, he can’t imagine not even having her in the same state anymore.

“I asked, they won’t let me. They don’t think she’ll watch me closely enough or whatever.”

“Well maybe you can stay with us! My parents love you and Jenny’s always wanted a sister- “

“Dan,” Vanessa says softly, putting a hand on his arm and cutting him off. “I’m sorry.”

Dan hangs his head down, feeling tears begin to fill his eyes. He wipes his cheeks with the back of his hand, Vanessa mercifully pretending like she doesn’t notice. Finally, he looks up again and makes eye contact with her for the first time in five minutes. “I don’t want you to go. I…I _love_ you, Vanessa.” She blinks back at him, apparently shocked. Before Dan knows what he’s doing, he’s leaning in and clumsily pressing his mouth to Vanessa’s.

Vanessa seems to kiss him back for several seconds, before she plants a hand on Dan’s chest and gently pushes him away. “I don’t…I don’t think that’s a good idea. Since I’m leaving and all.”

“So that’s it?”

“I’m really sorry,” Vanessa simply says again. She gives Dan a quick kiss on the cheek before climbing down the fire escape and disappearing into the night. It’s the last time Dan will speak to her for over a year.

Dan is never really sure why he did what he did that night and for the rest of his life whenever people ask him about his first kiss, he simply tells them it was on his fire escape and leaves it at that.

\---

Blair’s first time is unexpected, and she wakes up the next morning worried she’ll regret it for the rest of her life.

She had spent so long imagining every single aspect of what it would be like. How soft her new silk sheets would feel, the crisp red of the rose petals, the scents of the candles, the type of lingerie she would wear, even what Nate’s hair would look like.

Instead, Blair had none of that. She lost her virginity in the back of a moving limo while wearing nothing but an old slip, to a guy that wasn’t Nate but Nate’s best friend, a boy who took advantage of female students, slept with older women, and probably had STDs Blair had never even heard of.

Two hours before, she had thought she was going to marry Nate one day, but in what felt like a blink of an eye she was post-coital with Chuck Bass of all people.

“Are you sure?” he had asked her, and Blair had kissed him quickly, wanting to drown out a long-buried memory of Serena, wanting to get revenge on Nate, wanting to be anyone but Eleanor Waldorf’s daughter for the night. It hurt for only a few seconds and was over quickly, both of them already close after a night at Chuck’s new burlesque club.

Blair says absolutely nothing to Chuck as he drops her off at her building, already resolved to pretend it never happened, working on a plan to get Nate back. If he could go on pretending he was still a virgin for a year after Serena left, Blair can certainly do the same. She was always a much better liar than Nate anyway and now they’re even. An eye for an eye.

But it doesn’t feel like she finally got revenge on Nate. If anything, she feels worse than ever, breaking down into gasping sobs in the shower. They might be even, but it wasn’t supposed to be like this.

Blair will eventually fall for Chuck, and one day will be able to honestly say that she lost her virginity to someone she loved. But deep down, she knows nothing she felt for Chuck that night was love and wishes it could’ve been just a little like she had imagined.

\---

Dan’s first time is perfect, and he knows the next morning that he’ll look back on it fondly for the rest of his life.

He had never spent too much time imaging what it would be like, other than hoping it would happen before he was legally old enough to rent a car and that he would last longer than a minute. He goes in with no expectations, just some tips from the internet in the back of his head that he looked up after the whole “non-stop imagining Serena and Nate together” incident.

Dan had always known sex would be good, but his night with Serena could only be described as _magical_ , as corny as it was to admit. She had felt incredible, looked like an angel, and by some miracle, Serena actually came before he did.

As they lie amongst the fake Styrofoam snow, he looks up at the real snow falling above them. He has a strong urge to pull out a notebook and write about everything that just happened, but he ignores it, wanting to just stay in this moment with Serena as long as humanly possible.

With his arms wrapped around her, Dan realizes that this is the best Christmas he’s ever had and tells Serena just that. Serena agrees and Dan knows this is by far the most in love he’s ever been.

Dan and Serena eventually have to get up and sneak back home in the early morning light, sharing a final steamy kiss before they part.

As Dan walks back home after finding Serena a cab, he’s glad he had never really imagined what losing his virginity would be like. Nothing could compare to the real thing.

\---

Blair’s first kid never even gets to be born.

She had spent most of the summer in Monaco engrossed in her new royal duties, ignoring calls from Serena, emails from Humphrey, and not even letting herself think about Chuck. It’s not until the plane ride home that Blair realizes she hadn’t gotten her period once the whole time she was there. She goes to a drugstore all the way over in Queens, with giant sunglasses and a scarf wrapped around her head despite the August heat, praying that no one out here will recognize her.

She’s not surprised when the test comes out positive, but very disappointed, mainly in herself. On the one hand, having Louis as the father would be ideal, they could just move the wedding up and hopefully the Monégasque people will be too polite to comment on the timing. Yet a part of her can’t help but hope that Chuck is the father instead. She might not be enough on her own to make him a better man, but surely after everything with Bart, Chuck would make the effort for a child.

Blair’s not sure why she turns to Humphrey while she grapples with denial and the paternity test. She tries to justify it in her head that it’s just because Serena is out in California, but deep down she knows that even if Serena was in New York, Blair would’ve still leaned on him instead.

Things change once Blair gets official confirmation her child is Louis’. Her child is royalty and Blair feels she has no choice but to fully commit to Monaco and everything it entails, give this child the life they deserve. She knows what it’s like to have your father across an ocean and she doesn’t want her child to grow up the same way.

It’s hard though. Chuck has seemingly become a better man since he promised to move on from her, while Louis retreats further and further into the darkness. She keeps Humphrey at an arm’s length after reading a certain scene from _Inside_. She has a copy of the book buried deep in her nightstand, mostly unread, except for one passage she can’t help but read over and over again. She spends a lot of time trying to pretend she doesn’t know why.

When the Paparazzi invade her penthouse, she lies and tells herself she’s only going to Brooklyn for the seclusion. Humphrey takes her in without hesitation, helps her make a pro/con list, even helps her see Chuck again. As Chuck tells her he’ll love her baby just as much as he loves her, Blair feels a confusing mix of emotions. Relief that she can call off her engagement and stop pretending, hope that Chuck will finally change, and her child will still have a father that loves them, and something else deep in the pit of her stomach… _trepidation_.

After the car accident, Blair chalks up the trepidation she was feeling to some sort of premonition and ignores why she clings to Humphrey during the lowest point of her life. She tells herself it’s just because Humphrey is the one person who can understand what she’s going through, what with Georgina’s baby and all, but the truth is that Blair had totally forgotten about that until he had brought it up himself a week later.

Humphrey clears out her well-worn copy of _What to Expect When You’re Expecting_ , her list of baby names fit for a princess, and the silver Tiffany rattle tucked into the back of her closet. She tells him to throw it all out, but she knows he probably boxed it away and gave it to Dorota instead. Dan isn’t one to spend too much time in denial, while Blair has been doing it for years with no plans to stop.

That night she sobs into Humphrey’s shoulder. Sobs for the child she never got to meet. Sobs for Chuck, out of the woods now, but still healing after the accident. Sobs over the promise she had made to God. Sobs over Louis even; she can’t admit it out loud, but she knows what she’s doing to him isn’t fair either.

She leaves for Europe with Louis two days later and doesn’t tell Humphrey. She knows he’ll understand.

\---

Dan’s first kid technically isn’t even his.

Dan is horrified when Georgina first shows up at his door, positive that he has violated some sort of law of nature by breeding with a demon. Two minutes ago, he was just a teenage boy about to chase after one ex in order to get over another and now he’s a grown man about to become a father to a son.

He passes out and wakes up to Georgina standing above him, lazily fanning him with a magazine. She tells him she’s due in a month, that she has nowhere else to go, that she wants to raise the baby with him, but she doesn’t expect him to just drop everything and agree, especially after everything she put him through. Dan wonders if motherhood is softening Georgina, before realizing that’s probably impossible.

He thinks of his father, how he gave up his lifelong dream to raise him and Jenny, thinks of his mother and how much it hurt when she walked out of his life, and tells Georgina he’s all in.

Dan cuts off contact from everybody in his life except Nate, telling himself it’s just so he can get used to his new reality and commit one hundred percent to his unborn child. But he knows there’s a part of him with doubts; it’s why he holds off on signing the birth certificate when Milo is first born and why he asks Georgina to do a paternity test as soon as they can.

The birth is harrowing, and Dan sees parts of Georgina he had hoped never to see again, but then the doctor is putting Milo in his arms and asking Dan to cut the cord, and the moment turns in an instant from the grossest moment of Dan’s life to the happiest. He cries a little bit, making Georgina roll her eyes. “Pussy.” Dan doesn’t care.

Being a dad is terrifying and exhausting but Dan also wouldn’t trade it for anything in the world. The first six weeks of Milo’s life fly by, and Dan is surprised by how well everything with Georgina is going. But then his dad and Lily come back to town and Vanessa shows up at his door and then Georgina is outing Milo. Dan finally sees the results of a paternity test and signs the birth certificate, only to end up disappointed in himself when Georgina disappears the next day.

He barely has time to get adjusted to life as a single parent before he gets back together with Vanessa and his dad tells him Milo’s blood type doesn’t match his own and couldn’t be his. Dan is upset but deep down always knew this was a possibility.

With Georgina impossible to pin down, Dan resolves to raise Milo as his own anyway, Vanessa promising to be right there with him. But then Georgina comes back and takes him away and Dan is devastated. His dad and Lily and Vanessa want him to do nothing more but talk about his feelings, which is the absolute last thing Dan wants to do. So he does what he always does when he wants a distraction and goes to find Serena.

A year and a half later, he tells Blair the whole story and for the first time since it happened, he finally sees understanding dawn in someone’s eyes.

\---

Blair’s first wedding is a disaster.

The day starts out well enough. The church is beautiful, her tiara is flawless, and the new dress Vera made her fits perfectly. She still finds herself changing the subject when Serena remarks that Blair is getting everything she wanted and ignores the pit deep in her stomach as she brings up Serena’s fake relationship with Humphrey.

Things progress in a whirlwind from there. Before she knows it, Blair’s having a panic attack, then her mother is kicking everyone out of the bridal suite, then Blair’s confessing her love to Chuck, then Serena is asking Blair if she wants to run away (how typical), then her dad and Cyrus are walking her down the aisle, and then video of said love confession is sent out in a Gossip Girl blast. After she angrily confronts Chuck, who denies having anything to do with the video, Louis agrees to still go through with the wedding, bringing an end to the most hectic hour of Blair’s life.

She thinks she’s finally going to get a moment to catch her breath at the reception, but then Louis tells her he doesn’t love her anymore and their marriage will just be for show and that it was Humphrey of all people who wrote those beautiful vows. Blair feels like she just woke up from a bad dream, not recognizing her own life, not sure how it got to this point. Clearly being Blair Waldorf isn’t working anymore and she decides to pull a Serena: she runs away and brings Dan with her to boot.

Sitting in the airport wearing horrible polyester, Dan Humphrey by her side, Blair has never understood Serena more.

\---

Dan’s first wedding goes smoothly, all things considered.

Sure, Georgina and Jack get caught having sex in Blair and Chuck’s bedroom (Blair screams at Dorota to immediately burn the sheets) and Lily and his dad get into a massive fight out on the terrace that everyone awkwardly pretends they can’t hear, but Dan and Serena keep their focus solely on each other, trying to pretend like her ex isn’t staring wistfully after her or his ex isn’t hellbent on ignoring him, despite this being his wedding in her house.

Dan is glad they kept it small, but part of him wishes they had gone even smaller and just eloped. There’s too much bad blood in their family. Thank god Scott’s wife was 9 months pregnant and he wasn’t able to come – things were awkward enough without Dan and Serena having to be reminded they share a sibling. Dan’s mom also declined her invitation, with a less valid excuse, but Dan finds himself mostly relieved.

Once Georgina and Jack have slinked away and Lily and his dad are back with their respective partners, things calm down enough for Dan and Serena to share a final dance before they head out to the suite at the Plaza Jenny and Eric arranged for them. It’s not either of their styles, really, but they’ve both gotten good at pretending.

Serena kisses Dan long and hard before they go, whispering in his ear afterwards, “I’m glad it’s you.” Dan smiles and repeats the sentiment back, desperately wanting to mean it. Henry hugs him before they leave and as he holds the small bowtied boy, Dan glances up and catches Blair watching them.

For the first time since W, Dan is unable to read the expression on her face.

\---

Dan’s first divorce is quick, Serena not even bothering to show up to the proceedings. Dan isn’t surprised when he sees on Instagram that she’s run away to Thailand instead. Dan could get half of everything by default because of that, but he does what Serena probably knew he would and only keeps what was already his.

Blair’s first non-royal divorce is long and drawn out. Chuck has hired the best lawyers money can buy to fight for custody of Henry, but Blair has Cyrus by her side, a man she knows would fight to the death for her if necessary. Jenny agrees to testify against Chuck and even though Blair is sure Dan begged her to do it, she still gives Jenny a long hug anyway. To Blair’s surprise, Serena agrees to testify against Chuck as well. Afterwards, she calmly tells Blair on the courthouse steps that she’ll never forgive her for ruining her marriage and stealing her husband, but she wants nothing but the best for her godson, and the best thing for Henry would be to keep him far away from Chuck for the rest of his life.

Serena and Jenny’s testimony, alongside Blair’s own recollection of a decade of emotional and occasional physical abuse, is enough to get Blair full and sole custody. Chuck faces no real legal consequences beyond that, of course, but just knowing he can’t get to Henry or her anymore is enough for Blair. She buries her own guilt deep down and prays that the tabloid coverage of their divorce will be enough to stop any more women from getting hurt by him.

Nate happily takes a break from his mayoral duties to watch Henry for the weekend while Blair and Dan move into a refurbished townhouse on one of the fruit streets of Brooklyn Heights. Blair can see Lower Manhattan and the Statue of Liberty from her balcony and she laughs as she remembers being sixteen and feeling like Brooklyn was on a whole other planet. Now, Manhattan and all it represents still doesn’t feel far enough away.

Rufus comes by to give them his blessing, and Blair can’t help but eavesdrop as he pulls Dan aside before he leaves and warns him not to take this second chance for granted. Blair tears up, wondering why the Bass men have to ruin everything they touch. Her son is a Bass man too, but Blair stays up nights hoping that being raised by a Humphrey man will finally break the generational curse.

Dan takes to being an unofficial step-parent exceptionally well, teaching Henry how to throw a ball, reading to him before bed every single night, even letting Henry paint his nails after Blair leaves her make-up lying around one day. Nate and Jenny come by to see Henry often as well, Nate taking him to Yankees games, Jenny always with a new arts and crafts project for him to try. Blair is finally able to stop worrying that Henry will ever feel unloved.

Dan figures with the disastrous end to her marriages with both Louis and Chuck, the last thing Blair would want to do is get married again, and if she did, she would certainly make it clear, so he leaves it alone and pretends he’s fine with living unmarried to her for the rest of his life.

But one night before bed, Blair simply turns to him and says, “I’m pregnant.” Dan blinks back in shock, too happy and surprised to say anything back. A smirk tugs at the corner of Blair’s lips. “Uh, so Dan, are you going to do the honorable thing and marry me or what?”

Dan practically falls out of bed in his rush to get to the dresser, rummaging through the back of his sock drawer, finally finding the diamond ring he bought the day Blair told him she was leaving Chuck. Dan has been practicing his proposal to Blair for a decade now, but she only lets him get halfway through it before she pulls him off his knees and kisses him hard, falling back onto the bed and pulling him on top of her. Dan finds he doesn’t mind that he couldn’t finish, putting all his energy into finishing something else instead.

Neither Blair nor Dan ever have to sign any divorce papers again.

**Author's Note:**

> Blair, Serena, and Jenny testifying against Chuck was totally inspired by this [amazing fic](https://archiveofourown.org/works/29145597) that I highly recommend you check out, especially if Nate/Blair/Dan is your ot3 like me!


End file.
